family + business operations for parent entrepreneurs


We're Kevin + Courtney Gilroy: married best friends turned parent entrepreneurs. is the resource hub + like-minded community we were missing in our first days of new parenthood + business ownership.

Becoming a profitable stay-at-home family changed our life. Now, we help other current + soon-to-be parents have a healthy start to parenthood + entrepreneurship.

Learn more about our systems for running the business of family alongside the family business here or ask us questions here.




How We Knew We Were Ready to Start a Family

We’re sharing our list of pre-baby must-haves that helped us take a confident step into parenthood together.

Created by potrace 1.15, written by Peter Selinger 2001-2017
Reading Time: 5 minutes

How do you know when it’s the right time to have kids + start a family?

Some couples are on the same page + moving forward with baby-making full speed ahead. 

Other couples look at them with hesitation + reservation + start questioning how they could ever be so motivated + certain.

We were one of the “other couples” as we both knew we wanted to have children someday.

But while Kevin was ready to have a baby when he knew we were going to get married, Courtney was the one insisting upon having life in perfect order first.

Today, we’re sharing our list of pre-baby must-haves that helped us take a confident step into parenthood together.

No. 1 — Financial Planning for Parenthood


First, Courtney wanted to know that our home was safe. Her definition of safe was that:

  • we could foresee no major repairs needing to be made within the next 2 years;

  • she was comfortable being home alone with a baby there;

  • if our primary source of income (Kevin’s full-time 9-to-5 job) were to fall through, we would have some means of paying the mortgage + utilities for 6 months.

When we were paying our mortgage + utilities comfortably, in a decent neighborhood — with a 6-month-reserve for home stability — is when Courtney could be open-minded about conception.

Courtney’s preconception requisites seem like a tall order right out of the gate, but they were a motivating factor for her + Kevin. 

Securing home financially was the best prerequisite to parenthood we could’ve set for ourselves. Assuming a healthy mom + baby, the bare-bones basics we would need for parenthood was a safe home to shelter us. Everything else would be secondary.


Sometimes, mom + baby do have complications + as the old adage goes, “it is better to be safe than sorry.” 

Our second non-negotiable was to have well-rounded medical insurance or a designated “health money” plan that could cover what our insurance didn’t.

We contributed the max amount to our Health Savings Account (HSA) that would be matched by Kevin’s employer, then we made a pre-pregnancy preventative plan that conditioned both of us into optimal health before conceiving. 

Preventative care is much cheaper than curative care.

When we committed to maximizing health on the front-end of parenthood, we secured an easy, organic + low-cost conception, pregnancy, birth + postpartum experience as much as possible.

Stay-at-Home Motherhood

We were both raised by stay-at-home moms. We appreciate the life that gave us + had always known that this parenting style was a must for our someday family. 

We needed to be able to afford life on one income comfortably so that Courtney could have the postpartum recovery time her body needed. We needed the option to return to work in Courtney’s “spare” time without the pressure of a set start date.

For our generation, stay-at-home motherhood appears more like a luxury, but this is where the conversation of “needs” vs “wants” comes into play. 

In order for Courtney to be the happiest, healthiest mother possible for this child-to-be, she knew she needed to arrange our life in whatever ways allowed her to free up the pressure of a ticking clock. 

We made edits to our lifestyle to make this happen + where there’s a will, there’s a way. You can do it, too.

Happy couple looking at each other

No. 2 — Preconception Health Check


Kevin was using his gym membership while Courtney was following along to YouTube workout videos at home. 

We were in a fitness routine that had us feeling toned + relieved of stress. We felt good in our bodies + more confident than ever that Courtney could carry another life in addition to her own.


We felt like we understood what types of food made our bodies feel the best. 

We knew why we wanted to consume organically. We agreed that a commitment to organic nutrition was a must-have before conception + made the small changes to organic shopping before trying.

Vitamins & Supplements

If you do nothing else before conceiving a baby — please for the love of yourself + that baby — take the best prenatal vitamin you can afford. 

[Related: Our Daily Vitamins + Supplements]

Courtney cannot rave enough about MyKind Organics Prenatal Daily Multivitamin + their Daily Calcium + Magnesium Supplement. We had done our research + known what we wanted to have in Courtney’s system before trying.


Our sex life was great. 

We knew we could sustain the spontaneity + romance if sex ever started to feel mechanical.

We made a commitment to being honest about returning to romance if baby-making sex ever felt like a job. We think preparing for the adjustments in sex is a severely underrated part of starting a family.

Lady Parts

Courtney’s lady parts were healthy. This might seem obvious, but it’s worth mentioning! 

Courtney had an OB/GYN wellness appointment to rule out any pre-existing conditions. An all-around clean bill of health gave her confidence that she was primed for performance.

Happy couple

No. 3 — Emotional + Psychological Preparedness for Parenthood 

Many couples choose to start a family with emotions first. Who can blame them?

Choosing to make a baby is a bundle of emotions, let alone actually having your baby in your arms! Emotional is something you could be quite a lot.

However, letting emotions lead can get you in over your head. 

“You can’t hit the backspace on parenthood. Once you’re in it, you’re in it.”

For an irreversible decision, we felt we might as well prepare physically + financially first so that our emotions had a safe place to release + wouldn’t interfere as much with the smart logic required for healthy parenthood moving forward.

We felt ready to turn inward for a bit.

We had traveled a lot + felt okay with pausing our big travel adventures for this new parenting adventure (if one required the other).

We felt like we had more love to share.

We were happy with who we were going into parenthood + weren’t looking at parenthood as a way to love ourselves more. Stepping into parenthood was a way for us to give more.

Meeting your physical + financial prerequisites can actually take the mechanics out of parenthood so that you free up the space to feel all of the emotions.

You’re less stressed because you feel prepared, less confused because you have plans + less pressured because you know your options. 

The positive emotions you feel will be felt by the baby in utero. Give them all the goodness you can!

So now, we’d love to hear what you think: how did you know you were ready to start a family? 

What would you add to or take away from this list?

Come continue the conversation in our free community + until then, we’ll be cheering you on in health + wealth!